Would it be worth it to move to Montreal to live the Playboy+Europen lifestyle?

Well if you are not happy with NY taxes you will not like Canada. Taxes are out of site. Canada is a socialist country.

How cold is Montreal in January ? I prefer South Florida.

Look up merb.cc if your reasoning involves hookers, strippers and erotic massage.

Montreal is a different type of Canadian and IME they’re assholes, but then again people say the same thing about New Yorkers.

If I could just get up tomorrow and move anywhere (didn’t have to worry about a job, wife’s job, family close by) Toronto would be on my short lis of cities to move if the decision took strip clubs/massage/escorts into account.

@Dicky You might be right. Maybe the best plan would be to visit there for extended periods of time(mostly during the summers.

I traveled there for work many times and really loved the city and people. The people will react much more positively if you speak French. I say do it if Canada will give you the visa.

I lived in Montreal for 4 months in 2019 and am considering moving there as well. Not sure what you mean by European playboy life but I'd say go for it. However the Cost of living is not that much lower than NYC though and having a car will help with mongering.

Every city has its disadvantages. You know what New York’s are. You have yet to learn what Montreal’s are. My advice is to take a month off and spend a month getting to know Montreal before making a final decision.

The last time I was in Montreal the temperature was somewhere around -30.

On the one hand if you got that type of flexibility to just get up and move, then I don't see much of a downside - you can always move back or someplace else - or you could do as you subsequently posted and just go there for bits and pieces at a time and see if you'd truly like to live there - the 2nd-option is probably more prudent/flexible but the first option would allow you to experience more of the area as a live-in-citizen vs a visitor.

I'm not sure if the playboy/sex reputation of Montreal from yesteryear is really valid anymore.

The strip clubs are mostly expensive air dance factories. It does have a reputation for escorts, etc. but it's anyone's guess if that sticks post-Covid. As someone mentioned above, Canada is a socialist country and is very very locked down right now. Montreal actually has a curfew (yes a curfew) currently in effect. Everyone in the city has to be home by 9:30pm or they can be ticketed by police. There was a huge protest about it over the weekend.

I've always had fun when I've visited Montreal, but the time years ago that I went there for New Year's Eve with some friends was a mistake. So cold that when you went outside the inside of your notice almost instantly froze. I'll go back again, but never in the middle of winter.

Moving for paid sex? Wow. No thanks you.

@skibum You do you. Honestly, I could never get married nor have a wife. I strongly separate sex from "emotional connections."

@crosscheck When's the best month to go?

If you wanna live like a Playboy then move to a semi-impoverished country like Thailand

^ does Afghanistan come to mind? When we pull our soldiers out, you can join the Taliban and become a gentleman goat farmer

There are plenty of hookers in the US...

Beat - sex can be separate from an emotional connection, or a part of an emotional connection. I'd rather have both.